Bitcoin sets a new all-time high above $6,000 >>> READ MORE

Dump Your Losers for a Winning Cause

Gifting stock you no longer want is a real win-win for the holidays


End-of-year financial planning isn’t just for your tax return preparation, it can also be a great time to work on your retirement planning, too.

Of course, some planning moves cover both buckets. And because we still have no idea how the fiscal cliff is going to play out, developing a few investing strategies heading into the holiday season is worth the time.

One such strategy is a review of your portfolio. That’s critical to tax and retirement planning, particularly because the tax laws may change depending on what the ultimate fiscal cliff outcome is. Shaving off some long-standing appreciated stocks may make sense if you believe capital gains taxes will rise from the current 15%. And, of course, harvesting losers will save you up to $3,000 against those gains.

Also, any number of financial gurus are suggesting you run away from dividend stocks, but I’m not one of them for reasons laid out here.

While thinking about what to do with the stock portion of your portfolio, here’s an idea that might have some merit from a tax and retirement perspective — and that has the added benefit of “feeling good” during the holidays. Find those dogs you really don’t want to keep and instead of selling them for the measly $3,000 tax shelter, donate them to your favorite charity.

Gifting stocks (or mutual fund) shares that you’ve owned for more than one year boosts the savings on your tax return because the charitable-contribution deduction is the fair-market value of the securities on the date of the gift, not the amount you paid for the asset. If the stock is underperforming, you get the benefit of a full deduction for the sale value. If it’s been a winner, you never have to pay tax on the profit.

Here’s an example. As a past participant in Pitney Bowes‘ (NYSE:PBI) employee stock purchase program, I now own shares that I can’t value for tax purposes because I can’t access the cost basis data. My guess is that I’m underwater on the shares. I don’t want to cash them in without a basis, so I plan to gift them by year-end.

Voila! No guess on the gain or loss, full deduction on the current value of the shares and a feel-good day for me.

I suspect lots of retirees are in such a situation, with poorly performing stocks that you’ve owned for years but have fallen on hard times and might not recover in your lifetime. Names like JCPenney (NYSE:JCP), Hewlett-Packard (NYSE:HPQ), Best Buy (NYSE:BBY) and RadioShack (NYSE:RSH) come to mind right away.

Why not dump them in a philanthropic way? Tis the season for giving, and getting a little, too, makes it all the better.

Marc Bastow is an Assistant Editor at As of this writing he is long PBI, but not for much longer.

Article printed from InvestorPlace Media,

©2017 InvestorPlace Media, LLC